


Dear Diary

by VulpesNox



Category: Harry Potter - J. K. Rowling
Genre: Anal Sex, Bottom Harry, M/M, Masturbation, Porn With Plot, Sane Tom Riddle, Sex Magic, Teenage Tom Riddle, Underage Sex
Language: English
Status: Completed
Published: 2020-07-06
Updated: 2020-07-06
Packaged: 2021-03-04 23:08:49
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,551
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25114426
Author URL: https://archiveofourown.org/users/VulpesNox/pseuds/VulpesNox
Summary: Harry keeps Tom Riddle's diary in second year. After spending years talking to him, Harry decided he wanted to meet the other teen face to face.
Relationships: Harry Potter/Diary Tom Riddle, Harry Potter/Tom Riddle
Comments: 14
Kudos: 599





	Dear Diary

**Author's Note:**

> So I don't know if I'll write more for this or not! ^-^ but have another rarepair Harry sexy moment! Enjoy!

Harry resisted the urge to slam the door shut to his room, he was angry, however he wasn’t dumb enough to draw the unwanted attention from his aunt and uncle. So instead, he paced around his room, trying to settle the anger boiling under his skin, the itch he had to do something about his situation. 

His eyes caught a glimpse of the black leather bound book, the edge of it just visible from under his bed where he’d thrown it. 

Letting out a resigned sigh, Harry went first to his trunk, grabbed ink and a quill from inside, he sat himself on the floor, narrowing his eyes at the book, as if it were somehow offensive. In truth, it wasn’t the book itself that had Harry hesitating, but what it kept locked inside. 

Reaching out, Harry dragged it towards him, opening it to the first page; he felt a pang of guilt at what he saw written there. 

“Harry,” “Harry talk to me,” “Harry, are you okay?” “Harry?” “HARRY!” 

It was pages, and pages of text, asking if he was okay, cursing the ‘filthy muggles’ he lived with, promising a slow and painful death if they had even dared hurt him. 

Harry sighed, flipping to the first empty page he found, he dipped the quill in his ink and paused. There was so much to say, and Harry felt as if he should also apologise for vanishing the way he had, but after their last argument Harry hadn’t been able to bring himself to even look at the blasted book, let alone talk to the entity that resided within. 

Sighing again, Harry put the quill to the paper and simply wrote. “Hi, Tom,” he sat back and waited then. He wouldn’t blame Tom for ignoring him now, it had been two months since they had last ‘spoken’, and for all Tom knew, Harry had actually been killed by his aunt and uncle. 

Harry had made him worry, not that Tom would outright say it, but Harry knew. 

The minutes passed, and Harry remained sitting on the floor, he had nowhere else to go, and nothing better to do, so he waited for Tom, waited for his friend, waited for the only ‘person’ he felt a deep unbreakable connection with. 

Finally, after nearly an hour of waiting, all the previous words and ink vanished, replaced with a single response. 

“Where have you been?” 

Harry couldn’t keep the smile from his face as he practically dove at the diary, pulling it closer once more to scribble his hurried response. 

“I’m sorry, Tom, I was so mad after our last talk, and things have been…” Harry left it there, not sure if Tom would be willing to listen to his complaints about the Dursleys again, that is what had sparked their last argument. 

“Things have been what, Harry?” Tom demanded. 

“Nothing,” Harry wrote quickly. “Can I see you?” 

There was another long pause before Harry felt the familiar pull, he’d only done this a handful of times over the last few years. Ever since he’d found the diary, as a naive twelve year old boy who had been thrown headfirst into a magical world he was supposed to be part of, yet knew nothing about. 

It was one of the many things Harry and Tom could relate on, being thrown into this wonderful world that left your head spinning, and yet you were expected to keep up with everyone who had been raised knowing they were a witch or wizard; as such, Harry had found an unlikely friend in the boy trapped in the diary. 

Harry wasn’t the same naive boy he had once been though, he knew that Tom had been through so much more, and while he begrudgingly accepted the fact that Harry thought of him as a friend, the feeling wasn’t mutual. 

Stepping ‘foot’ into the greyed out world, Harry sighed as he realized where Tom had brought him this time, it was a cold dark dungeon, there was no fire in the fireplace, but a single chair in the middle of the room, and sat there was the lone figure of Tom Riddle. 

“So, you’re still upset with me?” Harry asked. 

“I think that question is one I should be asking you,” Tom said, idly turning a page in the book he appeared to be reading. 

Harry sighed and stepped forward. “I won’t apologise for being angry,” Harry said flatly. “But I will say I’m sorry for not talking to you, and for worrying you,” 

Tom looked up from his book then, eyeing Harry. “You mistook my words,” Tom said, closing the book. “You are a valuable tool to me, and it would have been frustrating to lose my only link to the outside world.” 

“Right, because one of these days, you’re going to steal my life essence and return to power as the Dark Lord,” Harry said dismissively. “I’ve been waiting for that for three years, Tom, and I’m still here.”

“Simply because you fascinate me,” Tom said, narrowing his eyes at Harry. 

“How fascinating could a twelve year old boy be?” Harry demanded, crossing his arms over his chest in challenge. “You don’t scare me, Tom, you never have,” he added. 

“And that, my dear Harry, is why you are so fascinating,” Tom stood up then, putting his book in the now vacant seat he stepped closer to Harry, slowly circling him. “Three years you say? That would make you, fifteen,” 

“Very observant of you,” Harry smirked, turning his head to look at the boy who in this form, was nothing more than a seventeen year old boy, someone who should have been looking forward to a bright future, but in his reality was facing two worlds that had rejected him, one where he had been born into, and left abandoned, another that had welcomed him with open arms, only to cast him aside and take away the only home he had ever known. In some ways, Harry saw his own future when he looked at Tom. 

“Your mind is wandering,” Tom said, and Harry blinked, lifting his gaze up to look at the handsome boy standing in front of him now. 

“You keep saying you can kill me, and… I don’t doubt that,” Harry admitted. “But I’m curious why you haven’t?” 

“Are you asking to die?” Tom questioned, and Harry shook his head quickly. 

“Don’t get me wrong, I’m not complaining that you haven’t killed me yet, I’m just asking… why?” Harry asked again, searching Tom’s face for any sign of what the boy might be thinking, but as usual, his expression was closed off and cold, never once hinting at what he was thinking or feeling in the moment. 

“You are a valuable asset to me, and there are others far more deserving to die than you,” Tom answered simply and Harry couldn’t stop the smile from spreading over his face, before suddenly wrapping his arms around Tom in a tight hug. 

“Release me this instant!” Tom demanded, shoving Harry back, glaring at him. “What has gotten into you, child?” 

“Sorry,” Harry said, but was still grinning. “It’s just,” Harry shook his head. “Forget it, sorry I showed my affection for you in a physical way, it won’t happen again,” 

“See that it doesn’t,” Tom insisted, returning to his chair, and Harry moved to sit in the second one that appeared, enjoying the glow of the fire that had started in the harth. “So, tell me what has happened in the last two months you said?” 

Harry nodded his head and began going into detail about what he’d been up to, about his aunt and uncle and their treatment of him, about the lack of communication between himself and the magical world. Harry spilled his heart out to the other boy as he usually did, the whole while he had Tom’s full attention, and just knew the other boy was truly listening to him, even if he didn’t say much. And it reminded Harry, that despite their differences, despite who Tom really was, who this Tom would grow up to be, it put Harry at ease knowing he had a friend like him. 

\------------x

Harry looked around the room slowly, checking things on the list before doing it again as he looked at the book that he had stumbled across in the restricted section. He always knew that that part of the library had some fascinating books, however he was more than a little surprised to have come across this one in particular. 

The title 99 Tedious Tricks for Transfiguration hadn’t given anything away about what was hidden in those pages, though the more Harry read, the more obvious it became that this was not the intended cover for this book. Unless McGonagall was adding some form of magical sex ed class to the curriculum. 

Harry shuddered at the thought, shaking his head to try and get himself to focus on the current task at hand. “Come on, think of something else…” he told himself, looking over at the diary that was laying open in the middle of the floor. He let his mind wander to the boy trapped in there, he had been thinking about him more often lately, wondering what it would be like to have him physically here. 

He knew he might still be a bit naive, he knew there was a very high chance that doing this, by setting Tom free, that not only would he be allowing Voldemort to return to the world, he’d be helping him do it. 

However, over the last few years, this past year in particular, Harry was finding it increasingly difficult to see the ‘pure evil’ that people seemed to fear. The only thing Harry saw when he looked at Tom, when he spoke to him, was another teenage boy who had been let down by the same people who were supposed to protect him. 

Strengthening his resolve, Harry stepped into the center of the room. “Well Tom, let’s get things started,” he said, putting the slip of paper down next to the diary, Harry stood up straight and started to loosen his tie, pulling the strip of fabric from around his neck, he tossed it aside. 

The rest of his clothes quickly followed, and soon he was standing naked in the circle of candles. He felt a chill run through him as he shuffled his bare feet on the stone floor, he felt very exposed, yet determined to see this through. Taking a deep breath Harry let it out slowly, reaching up he trailed a finger down his own neck, down to his chest. 

His hands were rough, calloused from years of working in Petunia’s garden, his upper body had a few faint scars, some from Vernon, but most were from Dudley. Letting out a huff of frustration Harry let his hands fall to his side. 

“Come on, Harry, you can do this, you’re a teenage boy for crying out loud,” he scolded himself, and tried again. He wasn’t getting very far though, as his body was refusing to react to his own touches, at least, not as fast as he would have liked. 

“Okay, let’s take a different approach…” he said, kneeling down slowly, he shuffled around until he was as comfortable as he could be on the stone floor, he looked at the diary when a thought occurred to him. 

Closing his eyes once more, he took a slow even breath. “Tom,” he breathed out, reaching up to try touching himself again, though this time, he tried to imagine that it was Tom’s fingers, gentle, curious, trailing ever so lightly down Harry’s neck, chest, pausing for a moment to brush over a sensitive nipple. 

Harry bit his lip as he ran his fingers over the hardening nub, before moving his hand across his chest to do the same to the other. He felt his cheeks heating up, and could feel the beginning sparks of pleasure traveling down his body, pooling in his lower abdomen as his cock twitched. 

“Tom,” Harry said again, keeping his touches teasing, finding every sensitive spot he knew, focusing mostly on his nipples for now as he rapidly came to realise that he liked the feeling, he tried pinching one, and he had to bite his lip harder as he tilted his head back letting out a muffled moan. 

Pressing the palm of his hand to his stomach, Harry slowly inched it down until his fingers brushed against his hardening cock. As he wrapped his hand around the flesh, he had to remind himself about the spell. 

Looking down Harry took a deep shuddering breath, letting go of the nipple he had been playing with he reached down and picked up the paper he’d written the spell on. He focused on the words, mouthing them first, he’d practiced pronouncing the spell, wanting to get this right, as he was sure he’d only get one shot at this. 

Slowly stroking his cock, pressing his thumb against the tip, he started teasing it, still picturing what it would feel like to have Tom touching him, or even Tom standing here watching him. That sent a new shiver down Harry’s spine and he started working his hand faster. 

When he felt precum start leaking from the tip, he shuffled forward, leaning over the diary he started chanting the spell. He felt a spike of pleasure shoot through him and he nearly lost his concentration, however he had read the warnings carefully, and he kept chanting, working his hand quickly over his cock that felt so much more sensitive. 

A tingling sensation danced across his skin and Harry moaned, biting his lip before chanting the spell again. Over and over again, working his hand over his leaking cock, feeling the precum leaking from the tip, Harry couldn’t bring himself to look down, knowing he was leaking onto the pages of the diary. 

He closed his eyes, focusing on the spell, and his hand, and the pleasure, and how hot he suddenly felt. 

“What is…” the new voice in the room had Harry’s eyes snapping open, afraid he’d been caught, that his locking charms on the door hadn't been enough. He didn’t stop muttering the spell under his breath though, even as he looked at the figure standing in front of him. 

“Harry?” Tom asked, sounding and looking confused, and perplexed to be suddenly standing there. 

Harry opened his mouth, debating on answering Tom, wanting to explain to him what was going on, but he stopped himself at the last second, instead chanting the spell again, lowering his head and arching his back as he worked his hand over his hard cock. The fact that Tom was standing there now, watching him, only made Harry feel hotter. 

The chanted spell continued, and Harry ended it with a loud moan, biting his lip as he felt his cock pulse almost painfully in his hand. He couldn’t stop though, stopping now would be dangerous, he had to keep going until he finished, however, even though it felt amazing, even though his cock was hard and throbbing, and Harry wanted to reach completion, it felt as if something was holding him back, keeping the pleasure from building more. 

As Harry started chanting again, he lifted his gaze, watching Tom’s feet as the other boy walked around the room slowly, pausing near the edge of the circle, Harry wanted to scream at him not to break the circle, not to leave it at all, though he didn’t need to, as Tom simply picked up the discarded book that Harry had found this spell in. 

Harry lifted his gaze further to watch as Tom looked through the pages of the book slowly, and he saw a growing understanding settle across Tom’s features, his brown eyes gleaming. 

“Harry, you foolishly brilliant child,” Tom chuckled, closing the book as he stepped forward again, his shoes echoing on the stone floor, he stopped in front of Harry once more, crouching down so that Harry didn’t have to crane his neck up so high to see him properly. “You understand what you’re doing?” he asked. 

Harry simply continued chanting, though he was speaking louder now, squeezed his cock harder and worked his hand faster. 

“You understand what will happen if you stop?” Tom asked, again, Harry didn’t answer with words, simply let his actions speak for themselves as he started working his hips lowly forward, slowly fucking into his hand. 

“Do you also understand that you missed a page of the spell,” Tom gestured to the book and Harry almost faltered, his eyes widening as he looked from Tom to the book, his breathing coming in quick gasps. “Without the second part to this spell, you would be stuck here like this, trapped in the endless loop of pleasure and pain, and the second you falter, the second you stop, you would be trapped with me in the diary,” Tom said. 

Harry felt like crying, he’d been stupid to think he could do this on his own, stupid to think he could free Tom from his prison. However, hearing this, knowing that he’d missed something drastic didn’t change things for him, he didn’t regret trying, he locked eyes with Tom again, slowing his hand down, preparing himself to stop, knowing that he’d failed already, so there was no point in continuing. 

“However, it just so happens that I know the second part of the spell needed,” Tom said, standing up, Harry stared, open mouthed as Tom started removing his own clothes. “Don’t stop chanting,” Tom ordered. 

Nodding his head Harry continued quickly, working his hand slowly still as he watched the other boy undress. He wanted to know what the second part of the spell intaled, however he trusted Tom, so he did as he was told and didn’t stop. 

“You’re very clever to have gotten this far, Harry, and to have worked out a way to pull me from the diary, without the loss of a life,” Tom praised, and Harry felt like smiling, though remained focused on his own task. “I can’t say if you fully understand what it is you’ve started, but we will discuss things, when we are finished.” 

Harry nodded his head slowly in understanding, staring at the other naked teen standing in the circle with him, Harry watched as Tom opened the book again, flipping to the correct page he started chanting something of his own. 

Harry gasped, his own chant faltering slightly, but he managed to salvage it in time, finishing it off quickly. He’d felt something strange, another wash of magic settled over him, and he wiggled his hips, whimpering in discomfort as he felt something slick building up between his ass cheeks. 

“Easy,” Tom said. “This is supposed to happen.”

Harry wanted to know how Tom was so sure about that, but didn’t question, just let him continue, as he shifted again, stroking his cock still, working more precum from the tip as it dripped down onto the diary still lying on the floor under him. 

The seconds ticked by and Harry could only feel himself getting more wet, it wasn’t an unpleasant feeling, just a forgin one, and he felt as if he needed something, his body ached for it, and Harry let out a needy whine. 

Tom ignored him though, continuing with his own chanting spell, until it tapered off naturally, and only then did the other boy close the book. Harry watched those feet as they walked around the circle, just out of his line of site and Harry felt his heart beating faster, fear and worry settling over him for a moment, until he felt the warm hand settle on his lower back. 

He jumped and turned his head around quickly, watching as Tom knelt behind him, his eyes drifted down to where he could just see the base of Tom’s cock. 

“You keep chanting, Harry, and whatever you do, don’t stop,” Tom ordered. Swallowing hard, Harry nodded his head slowly, realizing now he really hadn’t thought everything through fully, he opened his mouth and started the steam of chanting again. 

“That’s it, don’t stop,” Tom praised, his hand rubbing almost gentle circles on Harry’s back, easing some of the tense muscles there, though Harry couldn’t fully relax, especially when he felt something hard and heavy slip between his slick ass cheeks, rubbing along the crevice before finding his hole. 

Tom let out a breathy moan, one that was echoed by Harry as he moaned out the next sentence of the spell, the tight ring of muscles stretching easily and willingly to accommodate the thick cock that was penetrating him. 

“Don’t stop,” Tom said again, pushing himself forward, easing himself in and Harry felt the heat in his gut start building again. This is what his body needed, this is what he’d been missing, and he couldn't stop himself from pressing back, swiftly pulling the rest of Tom’s cock inside him. 

Tom cried out unexpectedly, but it was cut short as he gripped Harry’s hips and held him there. “As our bodies become one, so do our souls,” he said, starting up his own chanting that mirrored Harry’s. 

Harry did his best to hold still, feeling Tom’s cock pulsing deep inside him, twitching as it rested against his prostate, though Harry couldn’t help but push back, gasping as he felt the head of Tom’s cock press more firmly against the bundle of nerves. 

A dark chuckle filled the room, and Harry blushed, Tom didn’t say anything, just rubbed his hand over Harry’s back, and the younger teen understood the message, he had to be patient, they had to finish this first. 

Harry felt Tom’s other hand rest on his hip, and slowly the other teen started rocking his hips. He was hardly moving inside Harry, but it felt amazing, the gentle push and pull, the feeling of being filled so completely had Harry pulling at his cock harder and faster again, chanting louder, wanting to finish the spell. 

The hand on his hip snaked around to join his own, slender fingers entwined with his as the second hand wrapped around his cock, stroking along with Harry’s own hands. Tom leaned over him then, and Harry felt the warmth of his body against his own. 

Warm lips brushed against his ear, and Tom started whispering the chant to him. Harry didn’t know what Tom was chanting, and he didn’t care, it was intense, it was surreal, it was too much. As he worked his hand up to the tip of his cock, Tom pressed a finger against the head, working his thumb around it slowly, pressing down against the slit, his other hand moving to join the first, he cupped and squeezed Harry’s sack, and that was Harry’s undoing. 

He practically screamed the chant as he finally found release, his insides gripping the thick cock inside him as he came, his seed painting the pages of the diary, and only then did Tom start moving, hard and fast, hands on his hips now, gripping them, nails digging in as he fucked Harry quickly. 

Tom was still chanting, and Harry did his best to help, squeezing his inner muscles around the thick appendage. Harry leaned over, giving Tom a better angle to thrust at, Harry rested his head on the cool stone floor, pressing his scar there as he felt it start to burn, his body was torn between pain and pleasure, and he was only dimly aware of Tom reaching his own climax, and the hot seed flooding his insides. 

Reality started fading out, and blackness overtook his vision so suddenly that Harry fully collapsed, feeling warm and safe for the first time in his life and a set of arms wrapped around him and held him close. 

\--------x

It was the chill that woke him, the cool cloth rubbing over his forehead. Cracking open his eyes Harry blinked, frowning at the blurry structure of the room he was currently in. 

“Welcome back,” Tom said. 

Turning his head up, Harry blinked at the other teen, memory of what had happened came flooding back quickly and Harry sat up too fast, putting a hand on his head as the world swam dangerously. 

“Foolish child,” Tom scolded, easing Harry back down. “You’ve just completed a very powerful spell, your body is going to need time to recover,” 

“...did it work?” Harry asked, his throat feeling dry. 

A cool glass of water was pressed to his lips, and Harry sipped at it gratefully. 

“That depends,” Tom said. “What exactly were you trying to do?” he asked. 

Harry continued sipping at the water until the glass was nearly half empty, before turning his attention up to Tom once more. “I was trying to free you,” he explained. “Did it work? Or are we…” Harry trailed off, looking around to try and figure out if he recognized where they were. 

“We are in a secret room in the castle, I believe this was once the chambers of Salazar Slytherin,” Tom explained. 

“So, we’re still at Hogwarts?” Harry asked, smiling widely. “The spell worked? It actually worked?” 

“Yes, you succeeded in freeing me from that cursed place,” Tom said. “Do you understand fully what has happened though?” 

Harry shrugged. “Who cares, you’re free now!” Harry exclaimed. “If we hugged, I would seriously do that right now,” 

Harry was surprised when he felt long arms wrap around him then, pulling him close. “You sweet, idiot child,” Tom sighed, placing a gentle kiss to his forehead. 

“Tom…?” Harry asked in confusion. 

“You did more than free me, Harry, it appears you have set my soul free, in multiple ways, though I am unsure how it is possible…” Tom shook his head. “That will be a discussion for another time, for now, the basics of what you have done, what you achieved this evening, is you have bound me to you, and you to me, we now share this life Harry, your soul and mine are one,” 

Harry frowned. “What does that mean…” 

“In modern terms, we are now married,” Tom said and Harry’s eyes widened, his mouth falling open in utter shock, his look must have been priceless, as Tom suddenly threw his head back and laughed. 

It did have hints of the insanity that Harry had seen throughout the years, however it seemed more than that, it was a genuine laugh, one that morphed his features, and showed him for the human teen he truly was, and not the monster he was destined to become. 

“Tom, you’re scaring me,” Harry said, though he was mostly joking. 

“I am sorry, Harry,” Tom said, reaching up and brushing a thumb gently over Harry’s cheek. “Try and get some sleep, you will need it.”

Harry wanted to argue, wanted to demand answers, however he did still feel very drained and tired, and satisfied that the spell had worked, he decided he could deal with the consequences of his actions later, and if one of them really did mean he was stuck with Tom for the rest of his life, he decided that that was more than okay with him. 

END

**Author's Note:**

> I don't want to continue this as a chapter story, but I might write more oneshots for it.


End file.
